Sodium Hydroxide → 3-(3-(6-isopropoxypyridin-2-yl)-1H-indol-5-yl)-1,2,4-oxadiazol-5-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(3-(6-isopropoxypyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,2,4-oxadiazol-5-amine (220 mg, 0.44 mmol) in 1,4-dioxane (2.2 mL) was added 10% aq NaOH (1.1 mL) and the reaction was heated at 100° C. for 2 h. The mixture was cooled to RT and treated with ice cold water (2.2 mL). The precipitate was collected through filtration and the crude product was purified with preparative HPLC (eluent: 20-100% MeCN in water with 0.01% TFA) to give 3-(3-(6-isopropoxypyridin-2-yl)-1H-indol-5-yl)-1,2,4-oxadiazol-5-amine (25 mg, 17%). MS (ESI, pos. ion) m/z: 336.1 (M+1); 1H NMR (400 MHz, DMSO-d6): δ 11.75 (s, 1H), 9.10 (s, 1H), 8.16 (s, 1H), 7.75-7.64 (m, 4H), 7.52 (d, J=8.4 Hz, 1H), 7.41 (d, J=7.2 Hz, 1H), 6.51 (d, J=8.4 Hz, 1H), 5.54-5.52 (m, 1H), 1.44 (d, J=6.0 Hz, 6H).

Provenance & Evidence